When I worked with Rdio the RIAA sued them because users would make playlists named "Now that's what I call music < X >" with the same songs as the CDs. All the songs were fully licensed to be streamed on the service. The RIAA won those lawsuits.
edit: they might have actually settled, but the RIAA got what they wanted with no concessions
The RIAA doesn't seem to have a very good track record in cases that go to court, but the whole 'we're gonna sue you for eleventy billion dollars and destroy your life with our thousands of lawyers, but give us $20 right now and we'll call it even' seems to be quite effective.
You know, you might be right that in the end it was a settlement of sorts. I remember for a while they were fighting it specifically because it was about playlists (named groups of songs) which was not defined in the licensing in a way that clearly did or did not overlap with albums. The more I think about it, there was such a threat of refusing to renew licenses that it's possible they renewed with explicit language that prevented these playlists. I know for sure the playlists were purged. All said it was a hilarious amount of lawyer money over some of the dumbest CDs ever.
edit: they might have actually settled, but the RIAA got what they wanted with no concessions